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Water → 1-(6-(4-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-6-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl)-spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one

HRID 1846578
Notes
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Reaction equation

HRID 1846578 reaction equation
Cl.[NH:2]1[C:7]2[N:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[O:4][C:3]1=[O:17].Cl[C:19]1[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[N:22]=[C:21]([O:29][C:30]2[CH:39]=[C:38]([CH3:40])[C:33]3[NH:34][C:35](=[O:37])[O:36][C:32]=3[CH:31]=2)[CH:20]=1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[CH3:40][C:38]1[C:33]2[NH:34][C:35](=[O:37])[O:36][C:32]=2[CH:31]=[C:30]([O:29][C:21]2[N:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[N:24]=[C:19]([N:14]3[CH2:13][CH2:12][C:5]4([O:4][C:3](=[O:17])[NH:2][C:7]5[N:8]=[CH:9][CH:10]=[CH:11][C:6]4=5)[CH2:16][CH2:15]3)[CH:20]=2)[CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochlorideHCID 866639286-(6-chloro-2-trifluoromethyl-pyrimidin-4-yloxy)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 462439821-(6-(4-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-6-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl)-spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

90 mg (0.35 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 125 mg (0.36 mmol) 6-(6-chloro-2-trifluoromethyl-pyrimidin-4-yloxy)-4-methyl-3H-benzoxazol-2-one and 0.20 mL (1.16 mmol) DIPEA in 2.0 mL NMP were stirred for 14 h at 60° C. After cooling the reaction mixture was mixed with water and stirred for 30 min. The precipitate formed was suction filtered and dried.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customThe precipitate formed
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-cd3883df07424759b3a64dcfd6e126b7
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952014B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes